Amine co-initiators for radiation curable compositions

Abstract

A radiation curable composition comprising a curable compound, a photo-initiator and a co-initiator characterized in that said co-initiator is represented by Formula I, wherein MA is the residue of a mono- or oligofunctional Michael acceptor; L is a divalent linking group positioning the two tertiary amines in a 1-3 to 1-10 position, with the proviso that both amines are aliphatic; R1, R2 and R3 independently represent an optionally substituted alkyl group, an optionally substituted alkenyl group , an optionally substituted alkynyl group or an optionally substituted (hetero) alkaryl group; any two of R1, R2 and R3 may represent the necessary atoms to form a ring; any two of R1, R2 and R3 may represent the necessary atoms to form a ring with any of the atoms of the linking group L; n is an integer ranging from 1 to 6.

1. A radiation curable composition comprising a curable compound, a photo-initiator and at least one co-initiator, wherein said at least one co-initiator is represented by Formula I, wherein one of the two nitrogen atoms shown in Formula I, together with R2, R3, and L, forms a first aliphatic tertiary amino group and the other of the two nitrogen atoms shown in Formula I, together with L, MA and R1, forms a second aliphatic tertiary amino group; 
       
         
           
           
               
               
           
         
         wherein MA is a Michael acceptor residue formed by a Michael reaction of a Michael acceptor having 1 to 6 activated double bonds with an amine of the formula: 
       
       
         
           
           
               
               
           
         
         L is an C2 to C6 aliphatic divalent linking group which links the two nitrogen atoms in Formula I in a 1-3 to 1-10; n is an integer ranging from 1 to 6; 
         wherein R1, R2 and R3 in Formula I represent a C1 to C5 alkyl group; the Michael acceptor is selected from the group consisting of (meth)acrylates, (meth)acrylamides, vinyl sulfones, vinyl phosphonates, vinyl sulfonates, vinyl sulfonamides, maleimides, vinyl nitriles, vinyl ketones, vinyl aldehydes and vinyl sulfoxides. 
       
     
     
       2. The radiation curable composition according to  claim 1 , wherein said composition is a coating composition. 
     
     
       3. The radiation curable composition according to  claim 2 , wherein said coating composition is a varnish, primer, lacquer or an image recording layer. 
     
     
       4. The radiation curable composition according to  claim 1 , wherein said composition is a printing ink or fluid. 
     
     
       5. The radiation curable composition according to  claim 4 , wherein said printing ink or fluid is a radiation curable inkjet ink or fluid. 
     
     
       6. The radiation curable composition according to  claim 5 , wherein said radiation curable inkjet ink or fluid is a UV curable inkjet ink or fluid. 
     
     
       7. A radiation curable composition comprising a curable compound, a photo-initiator and at least one co-initiator, wherein said at least one co-initiator is represented by Formula I, wherein one of the two nitrogen atoms shown in Formula I, together with R2, R3, and L, forms a first aliphatic tertiary amino group and the other of the two nitrogen atoms shown in Formula I, together with L, MA and R1, forms a second aliphatic tertiary amino group; 
       
         
           
           
               
               
           
         
         wherein MA is a Michael acceptor residue formed by a Michael reaction of a Michael acceptor having 1 to 6 activated double bonds with an amine of the formula: 
       
       
         
           
           
               
               
           
         
         L is a divalent linking group which links the two nitrogen atoms in Formula I in a 1-3 to 1-10 position; 
         R1, R2 and R3 independently represent an optionally-substituted alkyl group, an optionally-substituted alkenyl group, an optionally-substituted alkynyl group or an optionally-substituted (hetero)alkaryl group; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring with any of the atoms of the linking group L; and
 n is an integer ranging from 1 to 6; 
 wherein said composition further includes a co-initiator having an aminobenzoate moiety. 
 
       
     
     
       8. The radiation curable composition according to  claim 7 , wherein MA includes a polymerizable group. 
     
     
       9. The radiation curable composition according to  claim 8 , wherein the polymerizable group is an acrylate group. 
     
     
       10. The radiation curable composition according to  claim 7 , wherein said composition is a coating composition. 
     
     
       11. The radiation curable composition according to  claim 10 , wherein said coating composition is a varnish, primer, lacquer or an image recording layer. 
     
     
       12. The radiation curable composition according to  claim 7 , wherein said composition is a printing ink or fluid. 
     
     
       13. The radiation curable composition according to  claim 12 , wherein said printing ink or fluid is a radiation curable inkjet ink or fluid. 
     
     
       14. The radiation curable composition according to  claim 13 , wherein said radiation curable inkjet ink or fluid is a UV curable inkjet ink or fluid. 
     
     
       15. A radiation curable composition comprising a curable compound, a photo-initiator and at least one co-initiator, wherein said at least one co-initiator is represented by Formula I, wherein one of the two nitrogen atoms shown in Formula I, together with R2, R3, and L, forms a first aliphatic tertiary amino group and the other of the two nitrogen atoms shown in Formula I, together with L, MA and R1, forms a second aliphatic tertiary amino group; 
       
         
           
           
               
               
           
         
         wherein MA is a Michael acceptor residue formed by a Michael reaction of a Michael acceptor having 1 to 6 activated double bonds with an amine of the formula: 
       
       
         
           
           
               
               
           
         
         L is a divalent linking group which links the two nitrogen atoms in Formula I in a 1-3 to 1-10 position; 
         R1, R2 and R3 independently represent an optionally-substituted alkyl group, an optionally-substituted alkenyl group, an optionally-substituted alkynyl group or an optionally-substituted (hetero)alkaryl group; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring with any of the atoms of the linking group L; and
 n is an integer ranging from 1 to 6; 
 wherein said curable compound is a vinyl ether acrylate. 
 
       
     
     
       16. The radiation curable composition according to  claim 15 , wherein MA includes a polymerizable group. 
     
     
       17. The radiation curable composition according to  claim 16 , wherein the polymerizable group is an acrylate group. 
     
     
       18. The radiation curable composition according to  claim 15 , wherein said composition is a coating composition. 
     
     
       19. The radiation curable composition according to  claim 18 , wherein said coating composition is a varnish, primer, lacquer or an image recording layer. 
     
     
       20. The radiation curable composition according to  claim 15 , wherein said composition is a printing ink or fluid. 
     
     
       21. The radiation curable composition according to  claim 20 , wherein said printing ink or fluid is a radiation curable inkjet ink or fluid. 
     
     
       22. The radiation curable composition according to  claim 21 , wherein said radiation curable inkjet ink or fluid is a UV curable inkjet ink or fluid. 
     
     
       23. A radiation curable composition comprising a curable compound, a photo-initiator and at least one co-initiator, wherein said at least one co-initiator is represented by Formula I, wherein one of the two nitrogen atoms shown in Formula I, together with R2, R3, and L, forms a first aliphatic tertiary amino group and the other of the two nitrogen atoms shown in Formula I, together with L, MA and R1, forms a second aliphatic tertiary amino group; 
       
         
           
           
               
               
           
         
         wherein MA is a Michael acceptor residue formed by a Michael reaction of a Michael acceptor having 1 to 6 activated double bonds with an amine of the formula: 
       
       
         
           
           
               
               
           
         
         L is a divalent linking group which links the two nitrogen atoms in Formula I in a 1-3 to 1-10 position; 
         R1, R2 and R3 independently represent an optionally-substituted alkyl group, an optionally-substituted alkenyl group, an optionally-substituted alkynyl group or an optionally-substituted (hetero)alkaryl group; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring; 
         any two of R1, R2 and R3 may represent the necessary atoms to form a ring with any of the atoms of the linking group L; and
 n is an integer ranging from 1 to 6; 
 wherein said photo-initiator is an acyl phosphine oxide or a bisacyl phosphine oxide. 
 
       
     
     
       24. The radiation curable composition according to  claim 23 , wherein MA includes a polymerizable group. 
     
     
       25. The radiation curable composition according to  claim 24 , wherein the polymerizable group is an acrylate group. 
     
     
       26. The radiation curable composition according to  claim 23 , wherein said composition is a coating composition. 
     
     
       27. The radiation curable composition according to  claim 26 , wherein said coating composition is a varnish, primer, lacquer or an image recording layer. 
     
     
       28. The radiation curable composition according to  claim 23 , wherein said composition is a printing ink or fluid. 
     
     
       29. The radiation curable composition according to  claim 28 , wherein said printing ink or fluid is a radiation curable inkjet ink or fluid. 
     
     
       30. The radiation curable composition according to  claim 29 , wherein said radiation curable inkjet ink or fluid is a UV curable inkjet ink or fluid. 
     
     
       31. A co-initiator represented by Formula V 
       
         
           
           
               
               
           
         
         wherein R7, R8 and R9 independently represent an optionally-substituted alkyl group, an optionally-substituted alkenyl group, an optionally-substituted alkynyl group or an optionally-substituted (hetero)alkaryl group; 
         L″ represents a C2 to C6 aliphatic divalent linking group; 
         A represents a di-or multifunctional linking group with a maximum functionality of 6; and 
         n is an integer ranging from 2 to 6.